It's a little embarrassing: I've worked in fashion for 15 years, and yet for most of that time, I haven't been obviously stylish. Which is not to say I'd been badly dressed—just a bit quietly dressed, perhaps. Years ago, I settled on a relatively hip, if limited, signature look of abstract floral dresses with, say, my trusty green military jacket. It allows me to wear designers I love while bestowing certain kindnesses upon my 5'3" "voluptuous meets athletic" frame (as described by my lovingly diplomatic husband). Adhering to this uniform from the runway sidelines—literally—I've watched one trend after another march past. Of course, it's worth noting that lots of fashion stalwarts pick a look and "make it their own," season in and season out. And, as a fashion writer, I like to believe my bosses have been more concerned with my content than my clothes; I'm expected to say something witty and on point about a collection, sparking trends with what I write, not what I wear. But I can't pretend I haven't felt, from time to time, as if I was missing out on some of the clotheshorse fun my profession is supposed to afford.

Then I got pregnant. Twice, actually, in 2008 and 2010. Both times, I was ecstatic but also experienced the usual mother-to-be agita; I lost sleep and, at times, my personality, a couples mentality with my husband, and control over my body. But, incredibly, fashionwise, pregnancy was a revelation. Dressing my new curves was a boon to my creativity, a way to take my mind off the not-so-fun parts of the experience (the cumbersome proportions, the physical discomfort, and the anxiety of making sure I didn't do anything to harm the baby, however unwittingly—more on this later).

Sound a little too good—and too convenient—to be true? It turns out lots of my friends experienced a similar sartorial liberation and moxie when they were pregnant. Linda Waddington-McEwan, design director of wovens for Tory Burch, was stylish beyond comprehension for the duration of her second pregnancy. Last year, in search of "reasonably priced items that looked like they had enough volume to accommodate my ever-changing shape," she tells me that she scoured eBay, unearthing past-season Prada, Gucci, and Chloé. "Prada did a great Ossie Clark–inspired collection years ago that is perfect for maternitywear," she notes, "and my Tory knitted tweed dresses became a staple." Linda also experimented with new labels. "I have never owned Missoni before but found it perfect for my shape, and the colors are bright but subtle." She avoided official maternitywear, bemoaning the prevalence of cheap jersey and excessive ruching as well as its lack of individuality.

Another woman I know, Donata Minelli Yirmiyahu, bypassed all maternity clothes (except unavoidable basics: jeans and hosiery), opting instead for the designs of Yigal Azrouël, Comme des Garçons, and Yohji Yamamoto. (Granted, as CEO of Yigal Azrouël, she had an inside track on a certain kind of draped, curve-friendly femininity.) "There are a lot of misconceptions of what a pregnant woman should wear; empire waists can so often be the most unflattering proportion," she says. "I love body-conscious silhouettes on pregnant women, even if you have to layer over it. A lot of maternity clothing never feels modern—it's always the same shapes and uninspiring prints." Donata theorizes that pregnant women are more experimental: "When you're desperate to find something to make you feel good, you're open to trying on a lot of different things. It can open up some ideas."

That might explain what happened to me. The first time I got pregnant, with my daughter, Asha, I was working at a magazine where the editors looked perfectly, artfully, chicly unkempt—a look I can't pull off, even when I'm not pregnant. And thanks to a sudden wave of celebrity fertility, I found myself bombarded with images of So-and-So wearing $350 maternity jeans (or regular ones in a whopping size 4) or That One in custom-made Lanvin.

But my understated uniform coupled with alien new dimensions? My first thought: This can't be good. For the first four months, I stuck with my regular clothes, relying increasingly on my most flowy dresses since my bust immediately swelled two cup sizes. (On an especially fun day at the New York lingerie shop Intimacy, I realized that my bra options were limited to feats of engineering that might have originated at MIT.)

Blessedly, though, my second trimester coincided with a megatrend of cocoon and tent shapes. So, right around the time I started pushing up my belts to empire heights, I did something that even my most fashion-obsessed, spendthrift friends couldn't fathom. I bought four Marni dresses: two floral, one ruffled hot pink, one in thick khaki canvas. The slightly voluminous shapes were flattering, especially with removable belts, and the fabrics—cotton or washed silk—were structured enough to help avoid frumpiness. By gestation's end, I would add always-flattering draped jersey looks from Anne Valérie Hash and Rick Owens and a fluid floral Chloé dress to the roster—three designers I'd previously never worn. I shopped with a sort of what-the-hell daring. If something didn't work on me, I figured I could blame it on my pregnant figure.

Imagine my surprise, at the pinnacle of roundness, at winning rave reviews from my colleagues and approving nods from other pregnant women. Instead of pitying my swollen ankles, everyone focused on the fact that at 36 weeks, I was wearing current season. This not only did wonders for my psyche; it also made my shopping spree—one that may sound foolhardy for a woman who hadn't bought so much as a baby onesie—seem fiscally defensible (or so I told myself): I wore every piece ad nauseam, up to delivery, and have continued to wear it all since, maybe with a belt.

It cannot go unremarked that my husband, friends, and coworkers told me daily that I looked amazing, whether it was true or not. That at 32, I had the wherewithal and self-knowledge to resist the impulse to buy shapeless, hide-everything sacks or the strangely cutesy things retailers offer moms-to-be (as if—what?—we want to dress like our future baby?). And that I was armed with a universal truth: One cannot criticize a pregnant woman's looks without being damned to hell for eternity. But my new daring was more than all this. It was almost chemical; the extra dose of estrogen coursing through my veins seemed to bring a confidence boost, manifested in my wardrobe.

A funny thing, though—not that I was laughing at the time—is that once my daughter was born, I promptly lost my newfound ability to put outfits together with anything close to originality or personality. With a newborn and a book project to contend with, I didn't have time to think about why. I just chalked up my pregnancy as 37 weeks in which, against all odds, everything—my hair, nails, skin, clothes—looked somehow right, and then went straight back to struggling to reconcile my love of fashion with the realities of my reconfigured body. Whatever air of confident invincibility I had amassed during my pregnancy chipped away while I was rushing home every day from work to relieve my nanny (yes, in itself a massive luxury). Two full years passed before I took off the weight I gained after having Asha.

And then, in 2010, literally as the last models walked off the spring runways, I found out (happily) that I was pregnant again. This time, there was nary a cocoon or sack shape in sight. Nothing but glam, high-waisted, '70s-inspired fare, which would look clownish on my short, zaftig self. Plus, with the expenses of parenting to contend with, Marni splurges seemed ill-advised. So I dutifully trooped out to a handful of mass-market maternity stores. But after a 10-minute crying jag in the dressing room of one chain, I realized that boxy, bowy blouses in ho-hum prints didn't make me look pregnant. They made me look...meh.

I also didn't care for the other fallback option: 10 months of head-to-toe black. I was not in mourning. I actually liked my body pregnant. It somehow rearranged my problem areas, and my burgeoning belly made my legs look skinny.

Hence my decision to venture even further outside my comfort zone. I learned that the prevailing body-con silhouette worked to my benefit, as long as it didn't include a cinched waist. Budget be damned, I bought extra-long printed Thakoon tops two sizes up—the length covered my stomach, and postpartum I had the side seams taken in. Ditto a few Rick Owens jersey tops and a Helmut Lang dress, all draped, snug in the right places, and done in abstract prints that camouflage. On a whim, I picked up a cotton devore T-shirt dress from 3.1 Phillip Lim that I'd never have touched normally, in that it's white and sheer. And back pain rendered me only really comfortable in heels—yes, really—which justified Jil Sander, Chloé, Tory Burch, and Theodora & Callum wedges.

The one maternity piece worth the investment proved to be a pair of J Brand jeans, which I wore constantly. I used to roll my eyes whenever I overheard colleagues extolling the virtues of the brand's every last seam. I get it now. J Brands suck in and support. They have low front bands, a high back-rise, and stretchy panels on the side so you still have the dignity of a front button and zipper.

By my ninth month, it seemed as if someone asked me daily if I was carrying twins. But I was still loath to give in, to reach for some shapeless, easy black sack—and not just because of my ego. Unfortunately, as with many women who are on the older side—at 36, I felt young, but according to medicine, I wasn't—my second pregnancy had its complications. A problem with my ovaries resulted in acute pain anytime I moved. To avoid emergency pre-term surgery if my ovaries ruptured and to manage the pain, doctors restricted my movement. Which caused gestational diabetes.

I couldn't pick up my daughter, exercise, eat anything with even a hint of carbs. All I could do was worry about protecting the pregnancy. Thinking about what to wear at least redirected some energy toward something I could control. It added a little levity to my day, and kept me from feeling sorry for myself.

Naturally, there were moments when my newfound sense of style teetered like a drunken game of Jenga, when I felt lumbering and swollen, not gloriously fertile and feminine. My husband fielded several midday e-mails in which the main conversation thread was simply, "I'm huge; I shouldn't be wearing this."

In the end, my son, Myles, was born perfectly healthy. And pregnancy proved to be empowering, in part because I did it on my own terms, not succumbing to the tyranny of the empire waist, the muumuu, or whatever else people thought I was "supposed to" wear just because I was having a baby. There may have been more of me, but I was also more "me" than ever.